N-tert-Butyl 4-Nitrophenylsulfonamide synthesis
- Product Name:N-tert-Butyl 4-Nitrophenylsulfonamide
- CAS Number:49690-09-7
- Molecular formula:C10H14N2O4S
- Molecular Weight:258.29
75-64-9
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Yield:49690-09-7 97%
Reaction Conditions:
Stage #1: tert-butylamine;4-Nitrobenzenesulfonyl chloride in tetrahydrofuran at 20; for 24 h;
Stage #2: with hydrogenchloride in chloroform;water;Acidic aqueous solution;
Steps:
1.A.a EXAMPLE 14-Amino-N-tert-butylbenzenesulfonamideMethod A: a) N-tert-Butyl-4-nitrobenzenesulfonamide
a) N-tert-Butyl-4-nitrobenzenesulfonamide To a solution of tert-butylamine (0.47 L, 6.4 mol) in THF (0.55 L) is slowly added, at 0 °C, a solution of 4-nitrobenzenesulfonyl chloride (50 g, 0.23 mol) in THF (0.55 L) and the resulting mixture is stirred for 24 h at room temperature.. The solvent is removed and the residue is taken up in a CHCl3/0.5 N HCl mixture, the layers are separated and the aqueous phase is extracted with CHCl3.. The combined organic extracts are washed with H2O and brine and dried over MgSO4.. The solvent is removed, yielding 56.3 g of a yellowish solid which is directly used in the next reaction (yield: 97%). Mp: 105-109°C; 1H-NMR (300 MHz, CDCl3) δ (TMS): 1.29 (s, 9 H), 5.07 (s, 1 H), 8.13 (d, J = 9 Hz, 2 H), 8.39 (d, J = 9 Hz, 2 H).
References:
EP1424329,2004,A1 Location in patent:Page 8
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